Rebecca Smith, Kendra Rick, Theresa Herbers

 

Proposed Synthesis of Compound D

Starting with bromoethane, we inserted a Mg ion into the C-Br bond with an Mg/THF reaction1.  The resulting compound was reacted with an aldehyde2, producing 2-butanol.  A bromide ion was substituted for the hydroxide group in a reaction with PBr₃ in pyridine6.  The compound was then able to insert a Mg ion with another Mg/THF reaction1, and then react with an aldehyde2 to produce 3-methyl-2-pentanol.  In an SN1 reaction, the hydroxide group was removed by reaction with H₂SO₄2 and was replaced by a fluoride ion.  This ion was eliminated by a NaOCH₃/CH₃OH reaction5 to produce the less substituted alkene.  Through a reaction with MCPBA8, the alkene was converted to an epoxide, which was then reacted with a Mg-activated ethyl bromide7 to produce the desired product, 3-methyl-4-heptanol.

 

 

1 Bruice. Organic Chemistry, pg. 456.

2 http://www.stolaf.edu/depts/chemistry/courses/toolkits/247/js/rxns/

3 Bruice. Organic Chemistry, pg. 436.

4 Bruice.  Organic Chemistry, pg. 364.

5 Bruice.  Organic Chemistry, pg. 396.

⁶ Bruice.  Organic Chemistry, pg. 457.

7 Bruice. Organic Chemistry, pg. 447.

8 Bruice. Organic Chemistry, pg. 802.